BiggerPockets Real Estate Podcast

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Investing in Office Buildings—A Beginner’s Guide

The Coming Collapse of Downtown Office Real Estate

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Kevin's LinkedIn

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-682

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681: Real Estate Horror Stories: Navigating Six-Figure Losses, Stabbings, and Sewer Problems Oct 30, 2022

Show notes

There’s a dark side of real estate no one talks about. Crime, destruction, theft, violence—you name it, we’ve dealt with it. With the spookiest day of the year coming close, we’re going to tell you all our terrible real estate tales. Everyone on podcasts and YouTube wants to show you how easy it is to invest, how it’s an assured path to wealth, and rarely what type of mistakes you can make. But we’re flipping the script, bringing in some of the best and brightest in real estate to show that the grass is usually greener where the septic tank is.

Today’s guests, who have all collectively succeeded at failing, are Andrew Cushman, Jamil Damji, and Matt Faircloth. If you’ve been a BiggerPockets listener, these names may sound familiar to you, but if you’re brand new, let us introduce you to these industry giants. Andrew is a multifamily expert and one of the smartest names in the game on screening and underwriting (analyzing) properties. Jamil built the nation’s largest wholesaling operation and is an expert guest on On the Market. And Matt, CEO of the DeRosa Group, literally wrote the book on Raising Private Capital.

But these titans of industry only made mistakes at the beginning of their careers, right? Not quite. They share today a selection of stories that will make you realize that the only successful investors are the ones who can both literally and figuratively weather a strong storm. And if you think it’s all cash flow and cruises for these investors, you couldn’t be more wrong.

In This Episode We Cover:

Why you should ALWAYS check out a property before you buy (and what happens if you don’t)

Becoming the "Sheriff" of your investment and how contractors can easily take you for a ride

1031 exchange mistakes and how to negotiate with a seller even when you’re on a time crunch

Always staying in your lane and trusting your gut when a deal doesn’t feel right

Paying more for insurance and how to financially prepare for a natural disaster

Why even with all the pain, real estate investing is the best wealth vehicle in the game!

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

BiggerPockets Podcast 661

Vantage Point Acquisitions

The DeRosa Group

Jamil’s YouTube

Book Mentioned in the Show:

Raising Private Capitalby Matt Faircloth

Connect with Matt, Andrew, & Jamil:

Andrew's BiggerPockets Profile

Jamil's BiggerPockets Profile

Matt's BiggerPockets Profile

Jamil's Instagram

Matt's Instagram

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-681

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680: Why Hosts Are Backing Away from Travel Sites and Building Direct Bookings w/Mark Simpson Oct 27, 2022

Show notes

Most people stumble into short-term rental investing. At some point, they realize a long-term rental, mother-in-law suite, or family cabin could become a revenue-generating, passive income machine. So what do they do? They go online to all the big travel sites, upload their listing, and start hosting. After a few months or years, they buy another short-term rental, and now, they’ve got multiple properties across a few different sites. The reviews are flowing, and the revenue with it. But one day, it stops.

This happened to Rob when his listing got locked—halting his revenue. Without much of a way to repair this, Rob started thinking of how he could host with autonomy and reduce the risk as his portfolio grew. Sooner or later, Rob and today’s guest, Mark Simpson, started talking. Mark, an expert in hospitality, knew that something like this would happen. It’s why Mark has been helping hosts build their own booking sites over at Boostly.

As a short-term rental expert, Mark helps hosts build an income stream that can’t be paused, limited, or removed. Instead, he and his team give hosts everything they need to get more bookings, pay fewer fees, and keep guests coming back for more. And, as the short-term rental space grows at lightspeed, Mark argues that hosts should start building out these direct booking sites now before it’s too late.

In This Episode We Cover:

The danger of solely hosting your short-term rentals on online travel agencies

How so many hosts find themselves “held hostage” by guests and travel sites

Building your “guest avatar” and modifying your vacation rental to fit your ideal guest

Guest screening tips and how to safely rent your property on your own website

Underrated upgrades to make to your short-term rental that massively boost bookings

Effortlessly converting guests online travel stays and into direct bookings

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

Stop Relying On Airbnb and VRBO and Build A Business You Control

4 Things You Need to Know Before Buying A Short-Term Rental

Boostly’s Property Management Software List

Books Mentioned in the Show:

Short-Term Rental, Long-Term Wealth by Avery Carl

The Book Direct Playbook by Mark Simpson

Connect with Mark:

Mark's Website

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-680

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679: Medium-Term Rentals: How to Get BIG Cash Flow Out of Small Properties w/Sarah Weaver and Zeona McIntyre Oct 25, 2022

Show notes

Medium-term rentals have seen growth like almost no other type of real estate. In the past, if you wanted high cash flow, you’d be hit with the headache of running a short-term or vacation rental. So, most investors who wanted to take the passive investing route stuck to regular, long-term rental properties. But, with interest rates higher than many of us have ever seen, most regular rental properties simply won’t cut it. Thankfully, there's a strategy that merges short and long-term rentals, with many of the combined benefits but few drawbacks.

The strategy is simple: buy a house, furnish it, and rent it out for over thirty days. Surprisingly, doing so will often get you double the rent as a regular rental property without the constant turnover of short-term rentals. Don’t believe us? Maybe Sarah Weaver and Zeona McIntyre can change your mind. They’ve been doing the medium-term rental strategy for years, and it’s what’s given them the financial freedom they enjoy today!

Sarah, shortly after finding out about the medium-term rental strategy, converted many of her long-term rentals into medium-term. Zeona, a former short-term rental owner, knew the high cash flow, low maintenance approach would help her live the nomadic lifestyle she loves. They detail exactly how they did it, what it takes to succeed, and how you can repeat the process in their new book, 30-Day Stay.

In This Episode We Cover:

The medium-term rental strategy explained and why it’s often a better bet than short-term rentals

Switching from short-term rentals to medium-term rentals and why the pivot makes sense

The best guests for medium-term rentals and why it isn’t always about traveling nurses

Which markets work best for this strategy and what bedroom/bathroom count has the highest ROI

Property management, maintenance, and how to make sure your medium-term rental succeeds

Analyzing a medium-term rental property and what extra costs to be aware of

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

BiggerPockets Podcast 229 w/Zeona

BiggerPockets Podcast 300 w/Zeona

BiggerPockets Podcast 563 w/Sarah

Furnished Finder Stats

Books Mentioned in the Show:

Profit like the Pros by Ken Corsini

Raising Private Capital by Matt Faircloth

SKILL by David Greene

30-Day Stay by Zeona McIntyre & Sarah Weaver (Use Code “ZEONA” or “SARAH” for a Discount)

Connect with Sarah & Zeona:

Sarah's Instagram

Zeona's Instagram

Sarah's BiggerPockets Profile

Zeona's BiggerPockets Profile

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-679

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678: Is the Buyer’s Market Back? How to Find Deals and Steals on the MLS w/Jamil Damji Oct 23, 2022

Show notes

Let’s be honest. The housing market has been a pain over the past few years. Sellers wouldn’t entertain any offer that wasn’t 10% over the listing price, real estate agents wouldn’t return your calls, and you may have thought that the time to buy rental properties was over. Fortunately, the tides have turned, and the seller’s market has almost overnight become a buyer’s market. Price drops are aplenty on the MLS, real estate agents want to be your best friend, and sellers desperately need to get their homes offloaded. This creates an opportunity for you to start buying deals at a discount.

Jamil Damji, America’s leading wholesaler, knows that now is the time to get properties under contract. He’s been an expert at off-market deal-finding for decades, but now, he says that on-market deals are becoming far easier to find. Combine his nationwide knowledge with David Greene’s agent expertise, and you have a masterclass on finding steals, not just deals, in today’s housing market.

David and Jamil go through eight different techniques you can use to find deals, lock them in at a low price, and grow your real estate portfolio, while everyone else is too scared to act. In times like these, when fear is at an all-time high, smart investors keep their cool, continue buying based on the numbers, and walk away far richer than the average investor. Interested in doing the same? Grab your notepad and write down these eight techniques. There’s a good chance you’ll be using them soon!

In This Episode We Cover:

How the housing market has shifted and whether or not we’ve become a buyer’s market

Off-market vs. on-market deal-finding strategies and which makes sense in 2022/2023

Using “emotional influence” to get a seller to agree to your terms as soon as possible

Building relationships with listing agents so they act as your ally in a deal

How to leverage “bad news” to turn frustration into motivation for a seller

Tell-tale signs of a motivated seller that will quickly get a deal done

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

BiggerPockets Podcast 677

BiggerPockets Podcast 667

These 20 Housing Markets Are Cooling the Fastest, According to Redfin

Connect with Jamil:

Jamil's BiggerPockets Profile

Jamil's Instagram

Jamil's YouTube

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-678

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677: How to Build an Income-Replacing, All Off-Market Rental Property Portfolio w/Taylor Wing Oct 20, 2022

Show notes

Financial freedom in two years? How can that be possible with high interest rates and higher home prices? If you’re looking at what’s on the MLS as the only deals around, you could be missing out on buying properties that could fast-track your journey to early retirement. Taylor Wing, unlike most investors, didn’t go the conventional route when building his rental property portfolio. But, walking the road less traveled has paid off significantly, as he has already found financial freedom in less time than it takes most investors to buy their first property!

Taylor’s career trajectory was cut and dry from the start. After graduating from West Point, he entered the Army and knew exactly how rankings, raises, and benefits would work from the day he started until the day he retired. This rigidity didn’t sit well with an entrepreneurial-minded, soon-to-be investor like Taylor. After his first house hack, and a very successful BRRRR, Taylor went full-throttle on investing.

Now, just two years later, he has a portfolio of over thirty rental units, a Rolodex full of private money lenders, and teams in multiple states ready to help him grow. So what sets Taylor apart from the rest? Aside from his resilience, Taylor chose to take action once he had enough information, instead of falling victim to analysis paralysis. If you follow Taylor’s advice, you too could grow a portfolio as fast as he did!

In This Episode We Cover:

Taking action, pushing past fear, and refusing to be stuck in analysis paralysis

Direct-to-seller marketing and how to find off-market real estate deals

Creative financing strategies, the subject to method, and no money down deals

Defining your “buy box” and red flags when looking for a BRRRR or rental property

Building your real estate team and the most important hire you can have

How to create an actionable plan to reach financial freedom in only a few years

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

Jamil's BiggerPockets Profile

Jamil's Instagram

Hear About “Reverse Flipping” with Ashley Hamilton

The 30-Something’s Guide to Financial Freedom

Try Follow Up Boss to Get More Real Estate Deals

Books Mentioned in the Show:

Financial Freedom with Real Estate Investing by Michael Blank

Traction by Gino Wickman

Connect with Taylor:

Taylor's BiggerPockets Profile

Taylor's Instagram

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-677

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676: Rob's Real Talk: What Running Short-Term Rentals at Scale REALLY Looks Like Oct 18, 2022

Show notes

The short-term rental game is not one to enter lightly. Regular rental property investors shudder at the constant turnover, consistent guest complaints, and far more intensive upkeep that vacation rental property owners pride themselves on. But is a week in the life of a self-managing short-term rental empire owner that bad? Well, maybe we’ll just have Rob Abasolo AKA Robuilt, YouTube’s go-to authority on vacation rental investing, answer this.

Rob has had a troubling week to put it lightly. From guests somehow deadbolting themselves out of their homes to ACs being frozen solid, sending vacationers to the wrong address, and almost obliterating a $20,000 pool, many things can go wrong in the realm of short-term rentals. But, is the profit worth the pain?

Dave Meyer from On The Market joins along this episode to act as Rob’s therapist/cheerleader as we go through a week’s worth of almost unbelievable events in the life of a vacation rental property owner. This episode highlights lessons learned from each mistake that you can use to build a better rental property portfolio, have a more seamless customer experience, and maybe get a little more “me and my burrito” time.

In This Episode We Cover:

Setting up fail-safes around your short-term rental so guests always have a way in

Why sticking to your guns isn’t always the best way to build a strong vacation destination brand

Supply chain shortages and how it’s severely delaying short-term rental owners

Why you should never fully drain a pool (unless you like paying $20,000+ in repairs!)

Using speed to your advantage and making guests feel heard as soon as a problem arises

Staying in contact with your team so you can solve problems smarter

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

Dave's BiggerPockets Profile

Dave's Instagram

The Ultimate Guide to Short-Term Rental Properties

How I Perfected the Process of Self-Managing My Rentals

Vacation Rentals Are Popular, But Are They Profitable?

Book Mentioned in the Show:

Short-Term Rental, Long-Term Wealth by Avery Carl

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-676

Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Check out our sponsor page!

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675: Seeing Greene: When Does It Make Sense to Refi with High Interest Rates? Oct 16, 2022

Show notes

Mortgage rates are up, which is good news for (almost) no one. Those who have built huge equity gains over the past few years now feel like they’re stuck at a crossroads. You could pull a cash-out refinance to buy another investment property, but with such high mortgage rates, is it better to wait out the market? This standoff between buyers, sellers, and the Federal Reserve have many investors confused about the next move to make. Thankfully, our in-the-field investing veteran, David Greene, is here to help.

Welcome back to another episode of Seeing Greene, where your host David answers questions on the spot from investors spanning every skill level. We’ve got video and text submissions this week, with topics ranging from whether to wait or buy now, how to push past negativity when you’re struggling to find deals, when to refinance while interest rates rise, asset protection basics, and much more. These in-depth answers from David will probably solve top-of-mind questions you may have too!

Want to ask David a question? If so, submit your question here so David can answer it on the next episode of Seeing Greene. Hop on the BiggerPockets forums and ask other investors their take, or follow David on Instagram to see when he’s going live so you can hop on a live Q&A and get your question answered on the spot!

In This Episode We Cover:

Whether to buy now or wait for a housing market correction

How to get out of a negative mindset when struggling to find deals

“Timing” your refinance to get the lowest rate possible (and whether or not it’s worth it)

What most investors get wrong about house hack “cash flow”

Asset protection basics and if an LLC is necessary for your first rental

Self-management vs. property management and when to trade money for time

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

Ask David Your Real Estate Investing Question

Jonathan's BiggerPockets Profile

Book Mentioned in the Show:

Real Estate by the Numbers by Dave Meyer & J Scott

Connect with Jonathan

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-675

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674: Investor Update: The "10 Deals on $20K/Year" Investor's Explosive Growth w/Ashley Hamilton Oct 13, 2022

Show notes

Ashley Hamilton is a landlord, multi-unit investor, reverse flipper, hard money lender, and everything else in between. You may recognize her name from episode 331, appropriately titled “10 Real Estate Deals on a $20K Waitress Salary,” which became one of the most popular BiggerPockets Real Estate Podcast episodes. If you haven’t heard of Ashley, here’s a quick rundown: As a teen mom, Ashley was working hard daily to provide for her kids. With only a $20K/year salary, she began buying rental properties, often in cash, in the Detroit area. The last time we chatted, Ashley had ten units. But now, things are very different.

Ashley knew that ten units and $7,000/month in cash flow was life-changing, but wanted to go even bigger. Since then, she’s rapidly expanded her rental property empire, growing her portfolio by many multiples and expanding into other businesses like consulting and hard money lending. She’s even developed her own version of the BRRRR strategy called “reverse flipping,” which makes high interest rates a non-issue when trying to refinance out of your property.

She gives some killer tips on keeping tenant turnover low, why paying taxes isn’t such a bad thing, and how betting on cities like Detroit can make you much wealthier. One surprising thing about Ashley is that she built the foundation of her portfolio on cash deals while making a below-poverty salary. So if you think money is the one thing stopping you from investing, Ashley will probably change your mind!

In This Episode We Cover:

Buying properties in cash and why leverage isn’t always the best move to make

What to do once you’ve hit financial freedom and building generational wealth

Going slow to build a property portfolio fast and “portfolio architecture”

Reducing tenant turnover and how Ashley kept 80% of her tenants over ten years!

The “reverse flip” strategy and why you should be on the lookout for PILFs

Investing even on a low salary and where cash flow can still be found

And So Much More!

Links from the Show

Listen to All Your Favorite BiggerPockets Podcasts in One Place

Learn About Real Estate, The Housing Market, and Money Management with The BiggerPockets Podcasts

Get More Deals Done with The BiggerPockets Investing Tools

Find a BiggerPockets Real Estate Meetup in Your Area

Hear Our First Interview with Ashley

Tenant Turnover Can Wreck Your Profits—Here’s the Simple Solution to This Costly Issue

Book Mentioned in the Show:

Buy, Rehab, Rent, Refinance, Repeat by David Greene

Connect with Ashley:

Ashley's BiggerPockets Profile

Work with Ashley Hamilton Consults

Ashley's Instagram

Click here to check the full show notes: https://www.biggerpockets.com/blog/real-estate-674

Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Check out our sponsor page!

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673: Beyond Cash on Cash: How Thinking Like an Investor Unlocks More Deals w/Dave Meyer & J Scott Oct 11, 2022

Show notes

What sets apart your everyday real estate investor from an investing expert? While novice investors are focused on cash flow only, veteran landlords focus on something worth much, much more. Thankfully, even if you’re just getting started on your investing journey, you don’t have to go through the hard work that experts like Dave Meyer and J Scott went through. Instead, you can hear their time-tested advice today, and grab their new book Real Estate by the Numbers!

J, a techie turned master flipper has written numerous books on estimating rehab costs, calculating real estate deals, and recession-proof investing. Dave, our VP of Data and Analytics and host of On the Market, has been head-down in housing market data for the past decade. These two real estate investing juggernauts combined their knowledge to write a book that lets every investor, no matter their skill level, find better deals, calculate profits smarter, and build wealth faster.

In this episode, we talk about calculating cash flow, ROI, and other metrics that may, or may not, matter as much as you’d think. You’ll hear how these two experts use much more than the numbers to define which deals are worth buying. After this episode, you may look at your portfolio differently, or even think about selling some of the properties you thought were “winners” before!

In This Episode We Cover:

The math behind the real estate deal and which metrics matter more than most

Calculating which properties work best for your portfolio

Defining your “buy box” and using it to filter through deals so you can build wealth faster

Why your property’s ROI (return on investment) might be even better than you think

How to start thinking like an investing expert and the lump sum vs. cash flow debate

Understanding the time value of money and how it’ll make you richer quicker

And So Much More!

Links from the Show